1-(4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-(1-methyl-1H-imidazol-2-yl)-1H-pyrimidine-2,4-dione

ID: ALA2367582

Cas Number: 134333-64-5

PubChem CID: 512321

Max Phase: Preclinical

Molecular Formula: C13H16N4O5

Molecular Weight: 308.29

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cn1ccnc1-c1cn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)[nH]c1=O

Standard InChI:  InChI=1S/C13H16N4O5/c1-16-3-2-14-11(16)7-5-17(13(21)15-12(7)20)10-4-8(19)9(6-18)22-10/h2-3,5,8-10,18-19H,4,6H2,1H3,(H,15,20,21)/t8-,9+,10+/m0/s1

Standard InChI Key:  LBTKTZHREVLEHD-IVZWLZJFSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  1  0  0  0  0  0999 V2000
    2.2960   -3.1123    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6014   -3.6935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9604   -3.8660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454   -4.5335    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8111   -2.4449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4219   -3.6073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2658   -4.4472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1165   -3.0261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0660   -1.6603    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9861   -2.4449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9739   -4.2204    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8344   -2.8928    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3986   -1.1754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7311   -1.6603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6414   -3.0644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1400   -3.9523    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7276   -3.8848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7508   -5.1147    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0535   -1.4053    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8024   -5.0274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3986   -0.3504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6841    0.0621    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  8  2  0
  3  1  1  0
  4  3  1  0
  5  1  1  1
  6  2  1  0
  7  2  1  0
  8  1  1  0
  9  5  1  0
  5 10  1  0
 11  6  1  0
 12  6  2  0
 13  9  1  0
 14 10  1  0
 15 12  1  0
 16  3  2  0
 17 11  1  0
 18  7  2  0
 14 19  1  6
 20 11  1  0
 13 21  1  1
 22 21  1  0
  7  4  1  0
 13 14  1  0
 15 17  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2367582

   1-(4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-(1-methyl-1H-imidazol-2-yl)-1H-pyrimidine-2,4-dione

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 308.29

Molecular Weight (Monoisotopic): 308.1121

AlogP: -1.42

#Rotatable Bonds: 3

Polar Surface Area: 122.37

Molecular Species: NEUTRAL

HBA: 8

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.47

CX Basic pKa: 3.12

CX LogP: -1.36

CX LogD: -1.37

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.64

Np Likeness Score: 0.27

References

1. Wigerinck P, Pannecouque C, Snoeck R, Claes P, De Clercq E, Herdewijn P..  (1991)  5-(5-Bromothien-2-yl)-2'-deoxyuridine and 5-(5-chlorothien-2-yl)-2'-deoxyuridine are equipotent to (E)-5-(2-bromovinyl)-2'-deoxyuridine in the inhibition of herpes simplex virus type I replication.,  34  (8): [PMID:1652017] [10.1021/jm00112a011]

Source

Source(1):

• Scientific Literature